GB785468A - Preparation of fluid polyvalent metal phenates - Google Patents

Preparation of fluid polyvalent metal phenates

Info

Publication number
GB785468A
GB785468A GB201/55A GB20155A GB785468A GB 785468 A GB785468 A GB 785468A GB 201/55 A GB201/55 A GB 201/55A GB 20155 A GB20155 A GB 20155A GB 785468 A GB785468 A GB 785468A
Authority
GB
United Kingdom
Prior art keywords
heated
water
phenol
mixture
methanol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB201/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Publication of GB785468A publication Critical patent/GB785468A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04Hydroxy compounds
    • C10M129/10Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/235Metal derivatives of a hydroxy group bound to a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/025Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027Neutral salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028Overbased salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/042Alcohols; Ethers; Aldehydes; Ketones
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06Perfluorinated compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088Neutral salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089Overbased salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/06Groups 3 or 13
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/08Groups 4 or 14
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/14Group 7
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/16Groups 8, 9, or 10

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

Oil-soluble polyvalent metal salts of phenolic compounds containing at least 10 carbon atoms for use as lubricating composition additives are produced, e.g. in mineral oil solution, by a process which comprises (a) preparing a solution of a polyvalent metal salt of the phenolic compound in a mixture containing a volatile organic solvent having a boiling point less than 170 DEG C., in which said salt is stable; (b) evaporating a major proportion of the volatile organic solvent from such solution at a temperature below the decomposition temperature of said polyvalent metal salt and (c) reacting the resulting material with from 0.1 to 2.5 moles. of water per mole. of polyvalent metal salt present. Phenolic compounds mentioned include alkylated phenols and naphthols and substitution products such chlorinated phenols and naphthols and phenol sulphides. Preferably, the phenolic compounds contain at least 10 aliphatic chain carbon atoms, preferably at least 20, in the form of alkyl or alkoxy radicals. Organic solvents mentioned include hydrocarbons, ethers, esters, alcohols and such ketones and aldehydes as are not reacted with phenolic compounds. Alcohols mentioned include methyl to iso-amyl and 2-methyl pentyl-4 alcohols. Basic metal salts may be prepared by forming the normal metal salts and after treatment with water and an excess of the appropriate metal alcoholate, further treating the product with water. Alternatively, the basic metal salt may be first prepared and treated with water. In examples: a mixture of magnesium methylate, methanol, octadecyl phenol and mineral oil is heated, concentrated and heated with water (1); in a similar process a polyisobutyl phenol containing an average of 32 carbon atoms per molecule is employed (2); dodecyl phenol is employed in a similar process (3); magnesium methylate in methanol is heated with the product of Example (2), the product is concentrated and treated with water (4); a mixture of sodium methylate, methanol octadecyl phenol and mineral oil is heated, zinc chloride in methanol is added and the mixture is concentrated and heated with water (5); polyisobutyl phenol is employed in a similar process (6); a mixture of sodium methylate, methanol, polyisobutyl-substituted phenol and zinc chloride is heated and concentrated, magnesium methylate in methanol is added and the mixture is heated, concentrated and again heated with water (7).ALSO:A method for producing a fluid, oil-soluble polyvalent metal salt of a phenolic compound, which phenolic compound contains a total of at least 10 carbon atoms, comprises the steps of (a) preparing a solution of a polyvalent metal salt of the phenolic compound in a mixture containing a volatile organic solvent having a boiling point less than 170 DEG C., in which said salt is stable; (b) evaporating a major proportion of the volatile organic solvent from such solution at a temperature below the decomposition temperature of said polyvalent metal salt; and (c) reacting with the resulting material from 0.1 to 2.5 mols. of water per mol. of polyvalent metal salt present. Phenolic compounds mentioned include alkylated phenols and naphthols and such substitution products as chlorinated phenols and naphthols and phenol sulphides. Preferably the phenolic compounds have in the molecule at least 10 aliphatic chain carbon atoms, preferably at least 20, e.g. in the form of alkyl or alkoxy radicals. Preferably such chains are derived from a polyisobutylene. Organic solvents mentioned include hydrocarbons, ethers, esters, alcohols and such ketones and aldehydes as are not reacted with phenolic compounds. Alcohols mentioned as suitable solvents include from methylto iso-amyl- and 2-methyl pentyl-4 alcohols. Basic metal salts may be prepared by forming the normal metal salts and after treatment with water and an excess of the appropriate metal alcoholate, further treating the product with water. Alternatively the basic metal salt may be first prepared and then treated with water. In examples: a mixture of magnesium methylate, methanol, octadecyl, phenol and mineral oil is heated under reflux, the product is concentrated under reduced pressure and the residue heated with water (1); in a similar process a polyisobutyl-substituted phenol containing an average of 32 carbon atoms per molecule is employed (2); dodecyl phenol is employed in a similar process (3); magnesium methylate in methanol is heated with the product of Example (2) and concentrated and treated with water (4); a mixture of sodium methylate, methanol, octadecyl phenol and minereal oil is heated, zinc chloride in methanol is added and the mixture is concentrated and the product is heated with water (5); a mixture of zinc chloride, sodium methylate, polyisobutyl phenol and mineral oil is heated, concentrated, and again heated with water (6); a mixture of sodium methylate, methanol, polyisobutyl-substituted phenol and zinc chloride is heated and concentrated, magnesium methylate in methanol is added and the mixture is heated, concentrated and again heated with water (7). Polyisobutyl phenol is prepared by heating phenol with a low molecular weight isobutylene polymer and a Friedel-Crafts catalyst, e.g. activated clay or aluminium chloride.
GB201/55A 1954-01-04 1955-01-04 Preparation of fluid polyvalent metal phenates Expired GB785468A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US785468XA 1954-01-04 1954-01-04

Publications (1)

Publication Number Publication Date
GB785468A true GB785468A (en) 1957-10-30

Family

ID=22144726

Family Applications (1)

Application Number Title Priority Date Filing Date
GB201/55A Expired GB785468A (en) 1954-01-04 1955-01-04 Preparation of fluid polyvalent metal phenates

Country Status (1)

Country Link
GB (1) GB785468A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2126602A (en) * 1982-08-16 1984-03-28 Maruzen Oil Co Ltd Process for the production of basic alkaline earth metal phenates
WO2017218657A3 (en) * 2016-06-17 2018-01-18 The Lubrizol Corporation Polyisobutylene-substituted phenol, derivatives thereof, and lubricating compositions containing the polyisobutylene-substituted phenol and its derivatives
US11572523B1 (en) 2022-01-26 2023-02-07 Afton Chemical Corporation Sulfurized additives with low levels of alkyl phenols
US11976252B2 (en) 2022-02-21 2024-05-07 Afton Chemical Corporation Polyalphaolefin phenols with high para-position selectivity

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2126602A (en) * 1982-08-16 1984-03-28 Maruzen Oil Co Ltd Process for the production of basic alkaline earth metal phenates
WO2017218657A3 (en) * 2016-06-17 2018-01-18 The Lubrizol Corporation Polyisobutylene-substituted phenol, derivatives thereof, and lubricating compositions containing the polyisobutylene-substituted phenol and its derivatives
EP3472274B1 (en) * 2016-06-17 2024-08-07 The Lubrizol Corporation Lubricating compositions containing a polyisobutylene-substituted phenol
US11572523B1 (en) 2022-01-26 2023-02-07 Afton Chemical Corporation Sulfurized additives with low levels of alkyl phenols
US11976250B2 (en) 2022-01-26 2024-05-07 Afton Chemical Corporation Sulfurized additives with low levels of alkyl phenols
US11976252B2 (en) 2022-02-21 2024-05-07 Afton Chemical Corporation Polyalphaolefin phenols with high para-position selectivity

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